# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1479943'
loop_
_audit_author_name
_audit_author_address
'Xiaoming Yang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2020-03-31 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;
_audit_creation_date             2016-05-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C6 H20 N14 Na2 O8'
_chemical_formula_sum            'C6 H20 N14 Na2 O8'
_chemical_formula_weight         462.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.2002(14)
_cell_length_b                   17.795(4)
_cell_length_c                   8.1862(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.91(3)
_cell_angle_gamma                90.00
_cell_volume                     986.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3330
_cell_measurement_temperature    153.1500
_cell_measurement_theta_max      27.4778
_cell_measurement_theta_min      1.1443
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8039
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6656
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.29
_diffrn_ambient_temperature      153.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 44.8364
	          2theta: -20.1920
scan:
	Number of images: 240
	           Slice: -110.0000 - 10.0000
	     Image width: 0.5000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 44.8364
	          2theta: -20.1920
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             2335
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0068
_diffrn_orient_matrix_UB_12      0.1084
_diffrn_orient_matrix_UB_13      -0.1001
_diffrn_orient_matrix_UB_21      0.0119
_diffrn_orient_matrix_UB_22      0.0369
_diffrn_orient_matrix_UB_23      0.0407
_diffrn_orient_matrix_UB_31      0.1213
_diffrn_orient_matrix_UB_32      0.0108
_diffrn_orient_matrix_UB_33      -0.0453
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           90.0000
_diffrn_source_power             4.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2066
_reflns_number_total             2252
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2252
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0553
_refine_ls_restrained_S_all      1.188
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0809P)²+0.9546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1470
_refine_ls_wR_factor_ref         0.1764
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
O4 \\sim O4A: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.01
Uanis(O4) \\sim Ueq, Uanis(O4A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
3. Others
 Sof(O4A)=Sof(H4AA)=Sof(H4AB)=1-FVAR(1)
 Sof(O4)=Sof(H4A)=Sof(H4B)=FVAR(1)
4.a Riding coordinates:
 O1(H1A,H1B), O2(H2A,H2B), O3(H3A,H3B), O4(H4A,H4B), N2(H2), O4A(H4AA,H4AB)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Na1 Na 0.40867(14) 0.46248(6) 0.65502(13) 0.0207(3) Uani 1 d . . . .
O1 O 0.1447(3) 0.42014(10) 0.3976(2) 0.0236(4) Uani 1 d A . . .
H1A H 0.0966 0.3776 0.4032 0.028 Uiso 1 d . . R .
H1B H 0.0422 0.4455 0.3496 0.028 Uiso 1 d . . R .
O2 O 0.6318(3) 0.42300(10) 0.5084(2) 0.0213(4) Uani 1 d . . . .
H2A H 0.5837 0.3858 0.4448 0.026 Uiso 1 d . . R .
H2B H 0.7429 0.4108 0.5787 0.026 Uiso 1 d . . R .
O3 O 0.6791(3) 0.53613(10) 0.8503(2) 0.0239(4) Uani 1 d A . . .
H3A H 0.6231 0.5740 0.8736 0.029 Uiso 1 d . . R .
H3B H 0.7513 0.5547 0.7990 0.029 Uiso 1 d . . R .
O4 O 0.1611(4) 0.48351(17) 0.7772(4) 0.0218(9) Uani 0.661(7) d A 1 . U
H4A H 0.1991 0.4924 0.8843 0.026 Uiso 0.661(7) d A 1 R .
H4B H 0.0791 0.4482 0.7593 0.026 Uiso 0.661(7) d A 1 R .
N1 N 0.4950(3) 0.27977(12) 1.3517(3) 0.0190(5) Uani 1 d A . . .
N2 N 0.4801(3) 0.23035(12) 1.4725(3) 0.0205(5) Uani 1 d A . . .
H2 H 0.4982 0.2443 1.5748 0.025 Uiso 1 d . . R .
N3 N 0.4628(3) 0.16152(12) 1.2466(3) 0.0194(5) Uani 1 d A . . .
N4 N 0.4703(3) 0.34052(12) 1.0154(3) 0.0215(5) Uani 1 d . . . .
N5 N 0.4764(3) 0.34522(12) 0.8529(3) 0.0214(5) Uani 1 d A . . .
N6 N 0.4977(3) 0.27702(12) 0.7992(3) 0.0197(5) Uani 1 d . . . .
N7 N 0.5068(3) 0.22634(12) 0.9236(3) 0.0186(5) Uani 1 d A . . .
C1 C 0.4888(3) 0.26711(13) 1.0534(3) 0.0147(5) Uani 1 d A . . .
C2 C 0.4837(3) 0.23622(13) 1.2179(3) 0.0147(5) Uani 1 d . . . .
C3 C 0.4610(4) 0.16146(14) 1.4086(3) 0.0205(5) Uani 1 d . . . .
H3 H 0.4478 0.1177 1.4701 0.025 Uiso 1 calc A . R .
O4A O 0.2330(9) 0.5277(4) 0.8287(8) 0.0247(17) Uani 0.339(7) d A 2 . U
H4AA H 0.1975 0.4923 0.8793 0.030 Uiso 0.339(7) d A 2 R .
H4AB H 0.3262 0.5551 0.8890 0.030 Uiso 0.339(7) d A 2 R .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Na1 0.0240(5) 0.0180(5) 0.0193(5) 0.0016(4) 0.0063(4) 0.0007(4)
O1 0.0228(9) 0.0185(9) 0.0280(10) 0.0025(7) 0.0068(8) -0.0013(7)
O2 0.0220(9) 0.0161(8) 0.0208(9) -0.0004(7) 0.0010(7) 0.0025(7)
O3 0.0292(10) 0.0194(9) 0.0233(9) -0.0015(7) 0.0092(8) 0.0012(7)
O4 0.0240(15) 0.0184(16) 0.0224(14) 0.0021(12) 0.0072(11) 0.0003(12)
N1 0.0246(10) 0.0188(10) 0.0155(10) -0.0003(8) 0.0092(8) -0.0020(8)
N2 0.0250(11) 0.0252(11) 0.0112(10) -0.0010(8) 0.0063(8) -0.0020(9)
N3 0.0236(10) 0.0166(10) 0.0183(10) 0.0008(8) 0.0075(8) -0.0010(8)
N4 0.0320(12) 0.0178(10) 0.0166(10) 0.0013(8) 0.0109(9) 0.0028(9)
N5 0.0279(11) 0.0203(11) 0.0182(10) 0.0016(8) 0.0106(9) 0.0024(9)
N6 0.0231(10) 0.0205(10) 0.0162(10) 0.0022(8) 0.0075(8) 0.0015(8)
N7 0.0232(11) 0.0189(10) 0.0148(10) 0.0006(8) 0.0078(8) 0.0003(8)
C1 0.0166(11) 0.0141(11) 0.0142(11) -0.0008(8) 0.0062(8) 0.0007(8)
C2 0.0138(10) 0.0165(11) 0.0129(11) 0.0014(9) 0.0035(8) 0.0003(8)
C3 0.0230(12) 0.0201(12) 0.0185(12) 0.0056(9) 0.0070(10) 0.0009(9)
O4A 0.026(3) 0.025(3) 0.026(3) 0.006(2) 0.011(2) 0.000(2)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Na1 Na1 3.497(2) 3_666 ?
Na1 O1 2.428(2) . ?
Na1 O2 2.400(2) 3_666 ?
Na1 O2 2.414(2) . ?
Na1 O3 2.438(2) . ?
Na1 O4 2.352(3) . ?
Na1 N5 2.584(2) . ?
Na1 O4A 2.489(6) . ?
O1 H1A 0.8401 . ?
O1 H1B 0.8399 . ?
O2 Na1 2.400(2) 3_666 ?
O2 H2A 0.8399 . ?
O2 H2B 0.8399 . ?
O3 H3A 0.8402 . ?
O3 H3B 0.8399 . ?
O4 H4A 0.8400 . ?
O4 H4B 0.8399 . ?
O4 H4AA 0.8012 . ?
N1 N2 1.355(3) . ?
N1 C2 1.322(3) . ?
N2 H2 0.8399 . ?
N2 C3 1.322(3) . ?
N3 C2 1.367(3) . ?
N3 C3 1.330(3) . ?
N4 N5 1.348(3) . ?
N4 C1 1.339(3) . ?
N5 N6 1.318(3) . ?
N6 N7 1.345(3) . ?
N7 C1 1.329(3) . ?
C1 C2 1.466(3) . ?
C3 H3 0.9500 . ?
O4A H4A 0.8587 . ?
O4A H4AA 0.8401 . ?
O4A H4AB 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Na1 Na1 82.26(6) . 3_666 ?
O1 Na1 O3 161.89(8) . . ?
O1 Na1 N5 102.61(8) . . ?
O1 Na1 O4A 103.92(16) . . ?
O2 Na1 Na1 43.57(5) 3_666 3_666 ?
O2 Na1 Na1 43.27(5) . 3_666 ?
O2 Na1 O1 82.48(7) 3_666 . ?
O2 Na1 O1 86.28(7) . . ?
O2 Na1 O2 86.84(7) 3_666 . ?
O2 Na1 O3 80.06(7) 3_666 . ?
O2 Na1 O3 87.97(7) . . ?
O2 Na1 N5 174.91(8) 3_666 . ?
O2 Na1 N5 93.51(7) . . ?
O2 Na1 O4A 86.19(14) 3_666 . ?
O2 Na1 O4A 166.77(17) . . ?
O3 Na1 Na1 81.79(6) . 3_666 ?
O3 Na1 N5 94.87(8) . . ?
O3 Na1 O4A 79.76(16) . . ?
O4 Na1 Na1 140.78(9) . 3_666 ?
O4 Na1 O1 86.31(9) . . ?
O4 Na1 O2 170.64(10) . . ?
O4 Na1 O2 97.84(9) . 3_666 ?
O4 Na1 O3 100.79(10) . . ?
O4 Na1 N5 82.55(9) . . ?
O4 Na1 O4A 22.58(15) . . ?
N5 Na1 Na1 136.56(7) . 3_666 ?
O4A Na1 Na1 128.78(14) . 3_666 ?
O4A Na1 N5 92.44(14) . . ?
Na1 O1 H1A 116.6 . . ?
Na1 O1 H1B 122.9 . . ?
H1A O1 H1B 101.4 . . ?
Na1 O2 Na1 93.16(7) 3_666 . ?
Na1 O2 H2A 112.1 3_666 . ?
Na1 O2 H2A 109.5 . . ?
Na1 O2 H2B 120.5 3_666 . ?
Na1 O2 H2B 112.0 . . ?
H2A O2 H2B 108.4 . . ?
Na1 O3 H3A 104.0 . . ?
Na1 O3 H3B 112.1 . . ?
H3A O3 H3B 102.9 . . ?
Na1 O4 H4A 116.7 . . ?
Na1 O4 H4B 113.3 . . ?
Na1 O4 H4AA 116.6 . . ?
H4A O4 H4B 106.5 . . ?
H4A O4 H4AA 0.4 . . ?
H4B O4 H4AA 106.8 . . ?
C2 N1 N2 103.1(2) . . ?
N1 N2 H2 120.8 . . ?
C3 N2 N1 109.7(2) . . ?
C3 N2 H2 129.0 . . ?
C3 N3 C2 102.2(2) . . ?
C1 N4 N5 104.8(2) . . ?
N4 N5 Na1 127.31(16) . . ?
N6 N5 Na1 123.56(16) . . ?
N6 N5 N4 108.6(2) . . ?
N5 N6 N7 110.2(2) . . ?
C1 N7 N6 104.3(2) . . ?
N4 C1 C2 123.2(2) . . ?
N7 C1 N4 112.1(2) . . ?
N7 C1 C2 124.7(2) . . ?
N1 C2 N3 114.0(2) . . ?
N1 C2 C1 121.8(2) . . ?
N3 C2 C1 124.1(2) . . ?
N2 C3 N3 111.0(2) . . ?
N2 C3 H3 124.5 . . ?
N3 C3 H3 124.5 . . ?
Na1 O4A H4A 104.7 . . ?
Na1 O4A H4AA 103.3 . . ?
Na1 O4A H4AB 98.4 . . ?
H4A O4A H4AA 2.3 . . ?
H4A O4A H4AB 115.3 . . ?
H4AA O4A H4AB 117.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Na1 Na1 N5 N4 144.67(18) 3_666 . . . ?
Na1 Na1 N5 N6 -44.7(2) 3_666 . . . ?
Na1 N5 N6 N7 -172.38(15) . . . . ?
O1 Na1 O2 Na1 82.66(7) . . . 3_666 ?
O1 Na1 N5 N4 -123.3(2) . . . . ?
O1 Na1 N5 N6 47.4(2) . . . . ?
O2 Na1 O2 Na1 0.000(2) 3_666 . . 3_666 ?
O2 Na1 N5 N4 55.9(10) 3_666 . . . ?
O2 Na1 N5 N4 149.7(2) . . . . ?
O2 Na1 N5 N6 -133.5(9) 3_666 . . . ?
O2 Na1 N5 N6 -39.6(2) . . . . ?
O3 Na1 O2 Na1 -80.16(7) . . . 3_666 ?
O3 Na1 N5 N4 61.5(2) . . . . ?
O3 Na1 N5 N6 -127.84(19) . . . . ?
O4 Na1 O2 Na1 120.3(5) . . . 3_666 ?
O4 Na1 N5 N4 -38.8(2) . . . . ?
O4 Na1 N5 N6 131.9(2) . . . . ?
N1 N2 C3 N3 0.2(3) . . . . ?
N2 N1 C2 N3 -0.1(3) . . . . ?
N2 N1 C2 C1 178.5(2) . . . . ?
N4 N5 N6 N7 -0.2(3) . . . . ?
N4 C1 C2 N1 -12.1(4) . . . . ?
N4 C1 C2 N3 166.4(2) . . . . ?
N5 Na1 O2 Na1 -174.91(8) . . . 3_666 ?
N5 N4 C1 N7 0.3(3) . . . . ?
N5 N4 C1 C2 -178.1(2) . . . . ?
N5 N6 N7 C1 0.4(3) . . . . ?
N6 N7 C1 N4 -0.4(3) . . . . ?
N6 N7 C1 C2 177.9(2) . . . . ?
N7 C1 C2 N1 169.8(2) . . . . ?
N7 C1 C2 N3 -11.7(4) . . . . ?
C1 N4 N5 Na1 171.77(16) . . . . ?
C1 N4 N5 N6 0.0(3) . . . . ?
C2 N1 N2 C3 0.0(3) . . . . ?
C2 N3 C3 N2 -0.3(3) . . . . ?
C3 N3 C2 N1 0.2(3) . . . . ?
C3 N3 C2 C1 -178.4(2) . . . . ?
O4A Na1 O2 Na1 -58.3(6) . . . 3_666 ?
O4A Na1 N5 N4 -18.4(3) . . . . ?
O4A Na1 N5 N6 152.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bwn19158
_database_code_depnum_ccdc_archive 'CCDC 1993945'
loop_
_audit_author_name
_audit_author_address
'Xiaoming Yang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2020-03-31 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;
_audit_creation_date             2019-04-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H7 N7 O2'
_chemical_formula_sum            'C5 H7 N7 O2'
_chemical_formula_weight         197.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.1663(10)
_cell_length_b                   10.327(2)
_cell_length_c                   7.6607(15)
_cell_angle_alpha                90
_cell_angle_beta                 105.39(3)
_cell_angle_gamma                90
_cell_volume                     394.06(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1372
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4739
_cell_measurement_theta_min      1.9721
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2548
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_min         3.946
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                867
_reflns_number_total             884
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         884
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.224
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0128P)²+0.3613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0943
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
2. Shared sites
{N3, C3}
3. Uiso/Uaniso restraints and constraints
Uanis(N3) = Uanis(C3)
4. Others
 Fixed Sof: N3(0.5) C3(0.5) H3(0.5)
5.a Riding coordinates:
 O1(H1)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7683(2) 0.06501(13) 0.15816(17) 0.0249(3) Uani 1 1 d . . . . .
H1 H 0.919968 0.082283 0.227175 0.030 Uiso 1 1 d R . . . .
N1 N 0.7033(3) 0.35267(14) 0.04294(19) 0.0208(3) Uani 1 1 d . . . . .
N2 N 0.6103(3) 0.24037(14) -0.03899(19) 0.0204(3) Uani 1 1 d . . . . .
C1 C 0.4978(3) 0.43150(17) -0.0232(2) 0.0200(4) Uani 1 1 d . . . . .
N4 N 0.2854(3) 0.37318(15) -0.1392(2) 0.0243(4) Uani 1 1 d . . . . .
N3 N 0.3633(3) 0.25205(16) -0.1464(2) 0.0234(4) Uani 0.5 1 d . . P A 1
C2 C 0.7671(4) 0.11979(17) -0.0077(2) 0.0231(4) Uani 1 1 d . . . . .
H2A H 0.689364 0.057469 -0.105758 0.028 Uiso 1 1 calc R . . . .
H2B H 0.953934 0.138218 -0.010661 0.028 Uiso 1 1 calc R . . . .
C3 C 0.3633(3) 0.25205(16) -0.1464(2) 0.0234(4) Uani 0.5 1 d . . P A 2
H3 H 0.260316 0.184752 -0.216468 0.028 Uiso 0.5 1 calc R . P A 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0200(6) 0.0254(7) 0.0257(7) 0.0051(5) -0.0005(5) -0.0025(5)
N1 0.0246(7) 0.0176(7) 0.0187(7) -0.0008(6) 0.0030(5) 0.0011(6)
N2 0.0204(7) 0.0197(7) 0.0192(7) -0.0004(6) 0.0021(5) 0.0008(6)
C1 0.0219(8) 0.0204(9) 0.0182(8) 0.0028(7) 0.0062(6) 0.0026(7)
N4 0.0220(7) 0.0223(8) 0.0273(8) 0.0023(6) 0.0045(6) 0.0030(6)
N3 0.0209(8) 0.0218(8) 0.0243(8) 0.0010(6) 0.0002(6) -0.0001(6)
C2 0.0262(8) 0.0179(8) 0.0251(9) -0.0004(7) 0.0066(7) 0.0031(7)
C3 0.0209(8) 0.0218(8) 0.0243(8) 0.0010(6) 0.0002(6) -0.0001(6)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8401 . ?
O1 C2 1.389(2) . ?
N1 N2 1.345(2) . ?
N1 C1 1.327(2) . ?
N2 N3 1.328(2) . ?
N2 C2 1.470(2) . ?
N2 C3 1.328(2) . ?
C1 C1 1.458(3) 3_665 ?
C1 N4 1.356(2) . ?
N4 N3 1.320(2) . ?
N4 C3 1.320(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 105.4 . . ?
C1 N1 N2 101.55(14) . . ?
N1 N2 C2 122.75(14) . . ?
N3 N2 N1 112.11(14) . . ?
N3 N2 C2 125.13(15) . . ?
C3 N2 N1 112.11(14) . . ?
C3 N2 C2 125.13(15) . . ?
N1 C1 C1 122.9(2) . 3_665 ?
N1 C1 N4 113.83(15) . . ?
N4 C1 C1 123.25(19) . 3_665 ?
N3 N4 C1 104.22(14) . . ?
C3 N4 C1 104.22(14) . . ?
N4 N3 N2 108.28(15) . . ?
O1 C2 N2 111.27(14) . . ?
O1 C2 H2A 109.4 . . ?
O1 C2 H2B 109.4 . . ?
N2 C2 H2A 109.4 . . ?
N2 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N2 C3 H3 125.9 . . ?
N4 C3 N2 108.28(15) . . ?
N4 C3 H3 125.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 N3 N4 0.2(2) . . . . ?
N1 N2 C2 O1 76.3(2) . . . . ?
N1 N2 C3 N4 0.2(2) . . . . ?
N1 C1 N4 N3 -0.4(2) . . . . ?
N1 C1 N4 C3 -0.4(2) . . . . ?
N2 N1 C1 C1 -178.8(2) . . . 3_665 ?
N2 N1 C1 N4 0.50(19) . . . . ?
C1 N1 N2 N3 -0.43(18) . . . . ?
C1 N1 N2 C2 -179.36(15) . . . . ?
C1 N1 N2 C3 -0.43(18) . . . . ?
C1 C1 N4 N3 178.9(2) 3_665 . . . ?
C1 C1 N4 C3 178.9(2) 3_665 . . . ?
C1 N4 N3 N2 0.10(19) . . . . ?
C1 N4 C3 N2 0.10(19) . . . . ?
N3 N2 C2 O1 -102.53(19) . . . . ?
C2 N2 N3 N4 179.11(15) . . . . ?
C2 N2 C3 N4 179.11(15) . . . . ?
C3 N2 C2 O1 -102.53(19) . . . . ?

_iucr_refine_instructions_details 
;
TITL bwn19158 in P2(1)/c
    bwn19158.res
    created by SHELXL-2018/3 at 15:13:03 on 18-Apr-2019
CELL 0.71073 5.1663 10.3269 7.6607 90 105.387 90
ZERR 2 0.001 0.0021 0.0015 0 0.03 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 10 14 14 4
EADP N3 C3
EXYZ N3 C3

L.S. 4
PLAN  5
SIZE 0.13 0.12 0.1
TEMP -120
ACTA
BOND $H
CONF
fmap 2
OMIT 0 2 3
OMIT 1 6 2
OMIT 0 4 0
OMIT 0 1 1
OMIT 3 2 6
REM <olex2.extras>
REM <HklSrc "%.\\bwn19158.hkl">
REM </olex2.extras>

WGHT    0.012800    0.361300
FVAR      16.52472
O1    4    0.768268    0.065013    0.158155    11.00000    0.01997    0.02538 =
         0.02571    0.00511   -0.00054   -0.00253
AFIX   3  0.8400
H1    2    0.919968    0.082283    0.227175    11.00000   -1.20000
AFIX   0
N1    3    0.703273    0.352667    0.042941    11.00000    0.02460    0.01763 =
         0.01867   -0.00076    0.00304    0.00106
N2    3    0.610316    0.240375   -0.038987    11.00000    0.02038    0.01971 =
         0.01922   -0.00035    0.00212    0.00079
C1    1    0.497849    0.431496   -0.023248    11.00000    0.02194    0.02035 =
         0.01817    0.00277    0.00615    0.00259
N4    3    0.285438    0.373176   -0.139214    11.00000    0.02200    0.02231 =
         0.02734    0.00228    0.00450    0.00298
PART 1
N3    3    0.363307    0.252050   -0.146427    10.50000    0.02088    0.02181 =
         0.02431    0.00097    0.00021   -0.00011
PART 0
C2    1    0.767107    0.119794   -0.007665    11.00000    0.02621    0.01793 =
         0.02515   -0.00040    0.00656    0.00310
AFIX  23
H2A   2    0.689364    0.057469   -0.105758    11.00000   -1.20000
H2B   2    0.953934    0.138218   -0.010661    11.00000   -1.20000
AFIX   0
PART 2
C3    1    0.363307    0.252050   -0.146427    10.50000    0.02088    0.02181 =
         0.02431    0.00097    0.00021   -0.00011
AFIX  43
H3    2    0.260316    0.184752   -0.216468    10.50000   -1.20000
AFIX   0
HKLF 4




REM  bwn19158 in P2(1)/c
REM wR2 = 0.0943, GooF = S = 1.224, Restrained GooF = 1.224 for all data
REM R1 = 0.0443 for 867 Fo > 4sig(Fo) and 0.0450 for all 884 data
REM 64 parameters refined using 0 restraints

END  
     
WGHT      0.0127      0.3615 

REM Highest difference peak  0.226,  deepest hole -0.187,  1-sigma level  0.050
Q1    1   0.5000  0.5000  0.0000  10.50000  0.05    0.23
Q2    1   0.4246  0.4161 -0.1158  11.00000  0.05    0.19
Q3    1   0.3540  0.3956 -0.0541  11.00000  0.05    0.18
Q4    1   0.6532 -0.0374  0.0265  11.00000  0.05    0.17
Q5    1   0.8693  0.3815  0.0834  11.00000  0.05    0.17

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0443 for 867 Fo > 4sig(Fo) and 0.0450 for all 2674 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.23, deepest hole -0.19
  REM Mean Shift 0, Max Shift 0.001.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0450
  REM R1_gt = 0.0443
  REM wR_ref = 0.0943
  REM GOOF = 1.224
  REM Shift_max = 0.001
  REM Shift_mean = 0
  REM Reflections_all = 2674
  REM Reflections_gt = 867
  REM Parameters = n/a
  REM Hole = -0.19
  REM Peak = 0.23
  REM Flack = n/a

  
;
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bn4450
_database_code_depnum_ccdc_archive 'CCDC 1993948'
loop_
_audit_author_name
_audit_author_address
'Xiaoming Yang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2020-03-31 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H8 K2 N14 O2'
_chemical_formula_weight         386.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.717(2)
_cell_length_b                   12.459(6)
_cell_length_c                   7.693(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.512(7)
_cell_angle_gamma                90.00
_cell_volume                     354.5(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    1507
_cell_measurement_theta_min      2.660
_cell_measurement_theta_max      31.497

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.810
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             196
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.8049
_exptl_absorpt_correction_T_max  0.9455
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3500
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0665
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         31.49
_reflns_number_total             1988
_reflns_number_gt                1653
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0193P)²+0.0960P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.08(4)
_refine_ls_number_reflns         1988
_refine_ls_number_parameters     113
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0700
_refine_ls_wR_factor_gt          0.0672
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
K1 K 0.52286(13) 0.57242(4) 0.65825(6) 0.01598(11) Uani 1 1 d . . .
O1 O 0.0410(5) 0.61460(14) 0.9151(2) 0.0204(4) Uani 1 1 d . . .
H1A H 0.0556 0.5626 1.0129 0.024 Uiso 1 1 calc R . .
H1B H 0.0446 0.6896 0.9576 0.024 Uiso 1 1 calc R . .
N1 N 0.5801(6) 0.46627(16) 0.3299(3) 0.0158(4) Uani 1 1 d . . .
N2 N 0.4281(6) 0.47236(16) 0.1639(3) 0.0172(4) Uani 1 1 d . . .
N3 N 0.4609(6) 0.37945(17) 0.0866(3) 0.0181(4) Uani 1 1 d . . .
N4 N 0.6379(6) 0.30974(17) 0.1968(3) 0.0173(4) Uani 1 1 d . . .
N5 N 0.9873(5) 0.38458(16) 0.6426(2) 0.0142(4) Uani 1 1 d . . .
N6 N 1.1385(6) 0.31259(17) 0.7606(3) 0.0159(4) Uani 1 1 d . . .
N7 N 0.9840(6) 0.21715(16) 0.5264(2) 0.0147(4) Uani 1 1 d . . .
C1 C 0.7094(6) 0.36583(18) 0.3437(3) 0.0116(4) Uani 1 1 d . . .
C2 C 0.8967(6) 0.32243(18) 0.5048(3) 0.0122(5) Uani 1 1 d . . .
C3 C 1.1352(7) 0.2153(2) 0.6917(3) 0.0162(5) Uani 1 1 d . . .
H3 H 1.2273 0.1528 0.7511 0.019 Uiso 1 1 calc R . .
H6 H 1.245(10) 0.336(3) 0.848(5) 0.043(11) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
K1 0.0162(2) 0.0164(2) 0.0150(2) -0.0006(2) -0.00064(16) 0.0020(2)
O1 0.0286(10) 0.0174(8) 0.0141(9) 0.0034(7) -0.0031(7) -0.0013(7)
N1 0.0206(10) 0.0145(10) 0.0111(10) 0.0010(8) -0.0039(8) 0.0013(8)
N2 0.0246(11) 0.0158(10) 0.0099(10) 0.0014(8) -0.0049(8) 0.0016(8)
N3 0.0209(10) 0.0209(11) 0.0113(10) 0.0001(9) -0.0058(8) 0.0023(9)
N4 0.0219(11) 0.0162(10) 0.0127(10) -0.0014(9) -0.0045(9) 0.0020(9)
N5 0.0206(10) 0.0131(9) 0.0079(10) -0.0002(8) -0.0043(8) 0.0012(8)
N6 0.0209(11) 0.0152(10) 0.0101(10) 0.0008(9) -0.0056(9) 0.0031(8)
N7 0.0194(10) 0.0128(9) 0.0113(10) -0.0003(8) -0.0017(8) 0.0015(8)
C1 0.0124(10) 0.0132(11) 0.0085(11) 0.0005(9) -0.0016(9) -0.0004(9)
C2 0.0126(11) 0.0125(11) 0.0114(11) 0.0000(9) 0.0003(9) -0.0007(10)
C3 0.0191(12) 0.0158(12) 0.0132(12) 0.0015(10) -0.0019(10) 0.0024(9)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
K1 O1 2.676(2) 1_655 ?
K1 O1 2.840(2) . ?
K1 N1 2.877(2) . ?
K1 N7 2.882(2) 2_656 ?
K1 N5 2.917(2) . ?
K1 N7 3.021(2) 2_756 ?
K1 N5 3.067(2) 1_455 ?
K1 N4 3.236(3) 2_656 ?
K1 K1 3.716(2) 1_455 ?
K1 K1 3.717(2) 1_655 ?
O1 K1 2.676(2) 1_455 ?
O1 H1A 0.9900 . ?
O1 H1B 0.9900 . ?
N1 C1 1.341(3) . ?
N1 N2 1.348(3) . ?
N2 N3 1.312(3) . ?
N3 N4 1.341(3) . ?
N4 C1 1.333(3) . ?
N4 K1 3.236(3) 2_646 ?
N5 C2 1.330(3) . ?
N5 N6 1.359(3) . ?
N5 K1 3.067(2) 1_655 ?
N6 C3 1.323(3) . ?
N6 H6 0.80(4) . ?
N7 C3 1.340(3) . ?
N7 C2 1.358(3) . ?
N7 K1 2.882(2) 2_646 ?
N7 K1 3.021(2) 2_746 ?
C1 C2 1.466(3) . ?
C3 H3 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 K1 O1 84.67(6) 1_655 . ?
O1 K1 N1 129.05(7) 1_655 . ?
O1 K1 N1 143.18(6) . . ?
O1 K1 N7 129.14(6) 1_655 2_656 ?
O1 K1 N7 78.54(6) . 2_656 ?
N1 K1 N7 87.41(6) . 2_656 ?
O1 K1 N5 78.53(6) 1_655 . ?
O1 K1 N5 126.31(6) . . ?
N1 K1 N5 60.08(6) . . ?
N7 K1 N5 147.46(6) 2_656 . ?
O1 K1 N7 78.69(6) 1_655 2_756 ?
O1 K1 N7 131.92(6) . 2_756 ?
N1 K1 N7 76.24(6) . 2_756 ?
N7 K1 N7 78.00(6) 2_656 2_756 ?
N5 K1 N7 94.09(7) . 2_756 ?
O1 K1 N5 126.66(6) 1_655 1_455 ?
O1 K1 N5 73.64(6) . 1_455 ?
N1 K1 N5 73.58(6) . 1_455 ?
N7 K1 N5 93.85(7) 2_656 1_455 ?
N5 K1 N5 76.74(6) . 1_455 ?
N7 K1 N5 149.05(6) 2_756 1_455 ?
O1 K1 N4 73.12(6) 1_655 2_656 ?
O1 K1 N4 56.06(5) . 2_656 ?
N1 K1 N4 138.96(6) . 2_656 ?
N7 K1 N4 57.62(6) 2_656 2_656 ?
N5 K1 N4 151.25(6) . 2_656 ?
N7 K1 N4 75.94(6) 2_756 2_656 ?
N5 K1 N4 124.76(6) 1_455 2_656 ?
O1 K1 K1 130.46(5) 1_655 1_455 ?
O1 K1 K1 45.79(4) . 1_455 ?
N1 K1 K1 99.11(4) . 1_455 ?
N7 K1 K1 52.67(5) 2_656 1_455 ?
N5 K1 K1 126.56(5) . 1_455 ?
N7 K1 K1 130.67(4) 2_756 1_455 ?
N5 K1 K1 49.82(4) 1_455 1_455 ?
N4 K1 K1 77.42(4) 2_656 1_455 ?
O1 K1 K1 49.54(5) 1_655 1_655 ?
O1 K1 K1 134.21(4) . 1_655 ?
N1 K1 K1 80.89(4) . 1_655 ?
N7 K1 K1 127.33(5) 2_656 1_655 ?
N5 K1 K1 53.44(4) . 1_655 ?
N7 K1 K1 49.33(4) 2_756 1_655 ?
N5 K1 K1 130.18(4) 1_455 1_655 ?
N4 K1 K1 102.58(4) 2_656 1_655 ?
K1 K1 K1 180.0 1_455 1_655 ?
K1 O1 K1 84.67(6) 1_455 . ?
K1 O1 H1A 114.5 1_455 . ?
K1 O1 H1A 114.5 . . ?
K1 O1 H1B 114.5 1_455 . ?
K1 O1 H1B 114.5 . . ?
H1A O1 H1B 111.6 . . ?
C1 N1 N2 103.97(19) . . ?
C1 N1 K1 114.59(15) . . ?
N2 N1 K1 138.27(15) . . ?
N3 N2 N1 109.33(19) . . ?
N2 N3 N4 110.2(2) . . ?
C1 N4 N3 103.99(19) . . ?
C1 N4 K1 102.45(15) . 2_646 ?
N3 N4 K1 135.56(16) . 2_646 ?
C2 N5 N6 101.8(2) . . ?
C2 N5 K1 113.23(15) . . ?
N6 N5 K1 135.27(15) . . ?
C2 N5 K1 126.10(15) . 1_655 ?
N6 N5 K1 104.62(14) . 1_655 ?
K1 N5 K1 76.74(6) . 1_655 ?
C3 N6 N5 110.5(2) . . ?
C3 N6 H6 131(3) . . ?
N5 N6 H6 117(3) . . ?
C3 N7 C2 101.9(2) . . ?
C3 N7 K1 130.66(16) . 2_646 ?
C2 N7 K1 114.01(15) . 2_646 ?
C3 N7 K1 102.57(15) . 2_746 ?
C2 N7 K1 131.88(15) . 2_746 ?
K1 N7 K1 78.00(6) 2_646 2_746 ?
N4 C1 N1 112.4(2) . . ?
N4 C1 C2 124.3(2) . . ?
N1 C1 C2 123.3(2) . . ?
N5 C2 N7 115.2(2) . . ?
N5 C2 C1 121.5(2) . . ?
N7 C2 C1 123.3(2) . . ?
N6 C3 N7 110.6(2) . . ?
N6 C3 H3 124.7 . . ?
N7 C3 H3 124.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 K1 O1 K1 180.0 1_655 . . 1_455 ?
N1 K1 O1 K1 -21.39(11) . . . 1_455 ?
N7 K1 O1 K1 48.25(6) 2_656 . . 1_455 ?
N5 K1 O1 K1 -108.45(6) . . . 1_455 ?
N7 K1 O1 K1 110.39(7) 2_756 . . 1_455 ?
N5 K1 O1 K1 -49.27(5) 1_455 . . 1_455 ?
N4 K1 O1 K1 106.78(7) 2_656 . . 1_455 ?
K1 K1 O1 K1 180.0 1_655 . . 1_455 ?
O1 K1 N1 C1 58.97(18) 1_655 . . . ?
O1 K1 N1 C1 -93.15(18) . . . . ?
N7 K1 N1 C1 -160.05(16) 2_656 . . . ?
N5 K1 N1 C1 18.64(15) . . . . ?
N7 K1 N1 C1 121.68(17) 2_756 . . . ?
N5 K1 N1 C1 -65.26(16) 1_455 . . . ?
N4 K1 N1 C1 170.22(14) 2_656 . . . ?
K1 K1 N1 C1 -108.51(15) 1_455 . . . ?
K1 K1 N1 C1 71.49(15) 1_655 . . . ?
O1 K1 N1 N2 -145.3(2) 1_655 . . . ?
O1 K1 N1 N2 62.6(3) . . . . ?
N7 K1 N1 N2 -4.3(2) 2_656 . . . ?
N5 K1 N1 N2 174.4(3) . . . . ?
N7 K1 N1 N2 -82.6(2) 2_756 . . . ?
N5 K1 N1 N2 90.5(2) 1_455 . . . ?
N4 K1 N1 N2 -34.0(3) 2_656 . . . ?
K1 K1 N1 N2 47.3(2) 1_455 . . . ?
K1 K1 N1 N2 -132.7(2) 1_655 . . . ?
C1 N1 N2 N3 1.3(3) . . . . ?
K1 N1 N2 N3 -156.08(18) . . . . ?
N1 N2 N3 N4 -0.8(3) . . . . ?
N2 N3 N4 C1 -0.1(3) . . . . ?
N2 N3 N4 K1 124.8(2) . . . 2_646 ?
O1 K1 N5 C2 -171.52(17) 1_655 . . . ?
O1 K1 N5 C2 113.95(16) . . . . ?
N1 K1 N5 C2 -22.38(15) . . . . ?
N7 K1 N5 C2 -19.9(2) 2_656 . . . ?
N7 K1 N5 C2 -93.94(16) 2_756 . . . ?
N5 K1 N5 C2 56.11(17) 1_455 . . . ?
N4 K1 N5 C2 -161.86(14) 2_656 . . . ?
K1 K1 N5 C2 56.11(17) 1_455 . . . ?
K1 K1 N5 C2 -123.89(17) 1_655 . . . ?
O1 K1 N5 N6 49.9(2) 1_655 . . . ?
O1 K1 N5 N6 -24.7(2) . . . . ?
N1 K1 N5 N6 -161.0(2) . . . . ?
N7 K1 N5 N6 -158.55(19) 2_656 . . . ?
N7 K1 N5 N6 127.4(2) 2_756 . . . ?
N5 K1 N5 N6 -82.5(2) 1_455 . . . ?
N4 K1 N5 N6 59.5(3) 2_656 . . . ?
K1 K1 N5 N6 -82.5(2) 1_455 . . . ?
K1 K1 N5 N6 97.5(2) 1_655 . . . ?
O1 K1 N5 K1 -47.64(5) 1_655 . . 1_655 ?
O1 K1 N5 K1 -122.16(6) . . . 1_655 ?
N1 K1 N5 K1 101.51(6) . . . 1_655 ?
N7 K1 N5 K1 103.95(10) 2_656 . . 1_655 ?
N7 K1 N5 K1 29.94(5) 2_756 . . 1_655 ?
N5 K1 N5 K1 180.0 1_455 . . 1_655 ?
N4 K1 N5 K1 -37.97(13) 2_656 . . 1_655 ?
K1 K1 N5 K1 180.0 1_455 . . 1_655 ?
C2 N5 N6 C3 0.5(3) . . . . ?
K1 N5 N6 C3 142.13(18) . . . . ?
K1 N5 N6 C3 -132.09(17) 1_655 . . . ?
N3 N4 C1 N1 0.9(3) . . . . ?
K1 N4 C1 N1 -143.01(17) 2_646 . . . ?
N3 N4 C1 C2 178.9(2) . . . . ?
K1 N4 C1 C2 34.9(2) 2_646 . . . ?
N2 N1 C1 N4 -1.4(3) . . . . ?
K1 N1 C1 N4 162.25(16) . . . . ?
N2 N1 C1 C2 -179.4(2) . . . . ?
K1 N1 C1 C2 -15.7(3) . . . . ?
N6 N5 C2 N7 -0.9(3) . . . . ?
K1 N5 C2 N7 -152.49(16) . . . . ?
K1 N5 C2 N7 117.3(2) 1_655 . . . ?
N6 N5 C2 C1 177.9(2) . . . . ?
K1 N5 C2 C1 26.3(3) . . . . ?
K1 N5 C2 C1 -63.9(3) 1_655 . . . ?
C3 N7 C2 N5 0.9(3) . . . . ?
K1 N7 C2 N5 146.30(16) 2_646 . . . ?
K1 N7 C2 N5 -118.3(2) 2_746 . . . ?
C3 N7 C2 C1 -177.9(2) . . . . ?
K1 N7 C2 C1 -32.5(3) 2_646 . . . ?
K1 N7 C2 C1 62.9(3) 2_746 . . . ?
N4 C1 C2 N5 174.3(2) . . . . ?
N1 C1 C2 N5 -8.0(3) . . . . ?
N4 C1 C2 N7 -7.0(4) . . . . ?
N1 C1 C2 N7 170.7(2) . . . . ?
N5 N6 C3 N7 0.0(3) . . . . ?
C2 N7 C3 N6 -0.5(3) . . . . ?
K1 N7 C3 N6 -137.38(19) 2_646 . . . ?
K1 N7 C3 N6 137.75(18) 2_746 . . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        31.49
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.077
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bwn19354
_database_code_depnum_ccdc_archive 'CCDC 1993947'
loop_
_audit_author_name
_audit_author_address
'Xiaoming Yang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2020-03-31 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;
_audit_creation_date             2019-07-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H4 K N7 O'
_chemical_formula_sum            'C4 H4 K N7 O'
_chemical_formula_weight         205.24
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.9924(8)
_cell_length_b                   12.192(2)
_cell_length_c                   7.7023(15)
_cell_angle_alpha                90
_cell_angle_beta                 95.44(3)
_cell_angle_gamma                90
_cell_volume                     373.22(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1407
_cell_measurement_temperature    163(2)
_cell_measurement_theta_max      27.4778
_cell_measurement_theta_min      1.6703
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.905
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2449
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         2.656
_diffrn_ambient_temperature      163.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.903
_reflns_number_gt                1600
_reflns_number_total             1614
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 721 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1614
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0279
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0477P)²+0.0792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0738
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
2.a Riding coordinates:
 O1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
K1 K 0.39578(13) 0.90224(3) 0.66111(6) 0.01866(16) Uani 1 1 d . . . . .
O1 O 0.3641(5) 0.90581(17) 1.0147(2) 0.0188(4) Uani 1 1 d . . . . .
H1 H 0.312919 0.954643 1.084398 0.023 Uiso 1 1 d R . . . .
N3 N -0.0705(6) 0.72523(19) 0.6630(3) 0.0168(5) Uani 1 1 d . . . . .
C3 C 0.6580(7) 1.1475(2) 0.8550(4) 0.0170(5) Uani 1 1 d . . . . .
H3 H 0.598670 1.118012 0.962066 0.020 Uiso 1 1 calc R . . . .
N2 N 0.7946(7) 0.5641(2) 0.7540(3) 0.0215(5) Uani 1 1 d . . . . .
C1 C -0.0010(6) 0.6478(2) 0.5484(3) 0.0134(5) Uani 1 1 d . . . . .
N1 N 0.8012(6) 0.6695(2) 0.7923(3) 0.0196(5) Uani 1 1 d . . . . .
N6 N 0.8201(6) 1.09250(18) 0.7396(3) 0.0168(5) Uani 1 1 d . . . . .
N4 N 0.2879(6) 0.76594(18) 0.3575(3) 0.0146(4) Uani 1 1 d . . . . .
N5 N 0.0808(7) 1.04704(19) 0.4003(3) 0.0203(5) Uani 1 1 d . . . . .
C2 C 0.8457(6) 1.1691(2) 0.6116(3) 0.0137(5) Uani 1 1 d . . . . .
N7 N 0.5894(5) 1.24994(19) 0.7999(3) 0.0143(4) Uani 1 1 d . . . . .
C4 C 0.5867(7) 0.8379(2) 1.1158(3) 0.0173(5) Uani 1 1 d . . . . .
H4A H 0.716042 0.882472 1.206321 0.021 Uiso 1 1 calc R . . . .
H4B H 0.748188 0.805100 1.040783 0.021 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
K1 0.0251(3) 0.0143(3) 0.0164(3) -0.0010(2) 0.00086(19) -0.0035(2)
O1 0.0276(9) 0.0160(8) 0.0137(8) 0.0012(8) 0.0057(6) 0.0036(8)
N3 0.0222(12) 0.0149(11) 0.0140(12) -0.0003(8) 0.0053(9) -0.0019(8)
C3 0.0218(12) 0.0130(11) 0.0164(12) 0.0014(9) 0.0032(10) -0.0033(10)
N2 0.0291(13) 0.0169(11) 0.0189(12) 0.0017(9) 0.0041(10) -0.0050(10)
C1 0.0167(11) 0.0106(11) 0.0128(12) -0.0008(10) 0.0000(11) -0.0011(10)
N1 0.0248(12) 0.0200(12) 0.0146(11) 0.0017(9) 0.0051(9) -0.0040(9)
N6 0.0206(12) 0.0143(11) 0.0154(11) 0.0002(9) 0.0016(8) -0.0013(9)
N4 0.0174(11) 0.0157(10) 0.0111(10) -0.0004(8) 0.0031(8) 0.0005(8)
N5 0.0277(13) 0.0159(11) 0.0176(11) -0.0011(9) 0.0030(9) 0.0034(9)
C2 0.0140(11) 0.0114(11) 0.0154(12) 0.0000(9) -0.0007(9) -0.0024(9)
N7 0.0171(11) 0.0138(10) 0.0126(9) 0.0001(8) 0.0043(8) -0.0012(8)
C4 0.0174(12) 0.0175(12) 0.0176(12) 0.0017(10) 0.0055(9) 0.0000(9)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
K1 K1 3.9924(8) 1_655 ?
K1 K1 3.9924(8) 1_455 ?
K1 O1 2.7385(18) . ?
K1 N3 3.032(2) 1_655 ?
K1 N3 2.851(2) . ?
K1 N1 3.374(3) . ?
K1 N6 3.360(3) 1_455 ?
K1 N6 2.902(2) . ?
K1 N4 2.868(2) . ?
K1 N5 2.873(3) . ?
O1 H1 0.8399 . ?
O1 C4 1.397(3) . ?
N3 C1 1.340(3) . ?
N3 N1 1.347(3) 1_455 ?
C3 H3 0.9500 . ?
C3 N6 1.329(4) . ?
C3 N7 1.340(4) . ?
N2 N1 1.318(4) . ?
N2 N5 1.348(4) 2_646 ?
C1 N5 1.338(3) 2_546 ?
C1 C2 1.455(3) 2_646 ?
N6 C2 1.369(3) . ?
N4 C2 1.326(3) 2_646 ?
N4 N7 1.364(3) 2_646 ?
N7 C4 1.467(3) 2_657 ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
K1 K1 K1 180.00(3) 1_455 1_655 ?
O1 K1 K1 81.93(5) . 1_455 ?
O1 K1 K1 98.07(5) . 1_655 ?
O1 K1 N3 85.14(7) . . ?
O1 K1 N3 96.04(7) . 1_655 ?
O1 K1 N1 77.38(6) . . ?
O1 K1 N6 82.01(7) . . ?
O1 K1 N6 73.33(6) . 1_455 ?
O1 K1 N4 143.37(7) . . ?
O1 K1 N5 128.84(7) . . ?
N3 K1 K1 130.80(5) . 1_655 ?
N3 K1 K1 45.38(5) 1_655 1_655 ?
N3 K1 K1 134.62(5) 1_655 1_455 ?
N3 K1 K1 49.20(5) . 1_455 ?
N3 K1 N3 85.42(7) . 1_655 ?
N3 K1 N1 69.92(7) . . ?
N3 K1 N1 23.50(6) 1_655 . ?
N3 K1 N6 93.65(7) . 1_455 ?
N3 K1 N6 169.37(6) 1_655 1_455 ?
N3 K1 N6 166.53(7) . . ?
N3 K1 N4 61.17(6) . . ?
N3 K1 N5 103.06(8) . . ?
N1 K1 K1 116.83(4) . 1_455 ?
N1 K1 K1 63.17(4) . 1_655 ?
N6 K1 K1 45.49(4) 1_455 1_455 ?
N6 K1 K1 55.67(5) . 1_655 ?
N6 K1 K1 134.51(4) 1_455 1_655 ?
N6 K1 K1 124.33(5) . 1_455 ?
N6 K1 N3 99.89(7) . 1_655 ?
N6 K1 N1 147.51(6) 1_455 . ?
N6 K1 N1 110.84(7) . . ?
N6 K1 N6 78.84(6) . 1_455 ?
N4 K1 K1 94.18(5) . 1_655 ?
N4 K1 K1 85.82(5) . 1_455 ?
N4 K1 N3 69.06(7) . 1_655 ?
N4 K1 N1 77.73(6) . . ?
N4 K1 N6 119.63(6) . 1_455 ?
N4 K1 N6 132.28(7) . . ?
N4 K1 N5 76.35(7) . . ?
N5 K1 K1 68.20(6) . 1_455 ?
N5 K1 K1 111.80(6) . 1_655 ?
N5 K1 N3 134.56(7) . 1_655 ?
N5 K1 N1 153.13(7) . . ?
N5 K1 N6 82.11(7) . . ?
N5 K1 N6 55.96(7) . 1_455 ?
K1 O1 H1 133.2 . . ?
C4 O1 K1 117.27(15) . . ?
C4 O1 H1 104.1 . . ?
K1 N3 K1 85.42(7) . 1_455 ?
C1 N3 K1 110.74(16) . . ?
C1 N3 K1 133.47(17) . 1_455 ?
C1 N3 N1 104.4(2) . 1_455 ?
N1 N3 K1 92.66(16) 1_455 1_455 ?
N1 N3 K1 132.86(18) 1_455 . ?
N6 C3 H3 124.6 . . ?
N6 C3 N7 110.9(2) . . ?
N7 C3 H3 124.6 . . ?
N1 N2 N5 110.3(2) . 2_646 ?
N3 C1 C2 124.3(2) . 2_646 ?
N5 C1 N3 112.5(2) 2_546 . ?
N5 C1 C2 123.2(2) 2_546 2_646 ?
N3 N1 K1 63.84(14) 1_655 . ?
N2 N1 K1 138.9(2) . . ?
N2 N1 N3 109.1(2) . 1_655 ?
K1 N6 K1 78.84(6) . 1_655 ?
C3 N6 K1 148.56(18) . 1_655 ?
C3 N6 K1 103.33(17) . . ?
C3 N6 C2 102.2(2) . . ?
C2 N6 K1 118.50(16) . . ?
C2 N6 K1 104.02(16) . 1_655 ?
C2 N4 K1 113.69(16) 2_646 . ?
C2 N4 N7 102.5(2) 2_646 2_646 ?
N7 N4 K1 140.25(16) 2_646 . ?
N2 N5 K1 122.54(18) 2_656 . ?
C1 N5 K1 117.28(17) 2_556 . ?
C1 N5 N2 103.7(2) 2_556 2_656 ?
N6 C2 C1 123.7(2) . 2_656 ?
N4 C2 C1 121.5(2) 2_656 2_656 ?
N4 C2 N6 114.8(2) 2_656 . ?
C3 N7 N4 109.6(2) . 2_656 ?
C3 N7 C4 129.3(2) . 2_657 ?
N4 N7 C4 121.1(2) 2_656 2_657 ?
O1 C4 N7 112.0(2) . 2_647 ?
O1 C4 H4A 109.2 . . ?
O1 C4 H4B 109.2 . . ?
N7 C4 H4A 109.2 2_647 . ?
N7 C4 H4B 109.2 2_647 . ?
H4A C4 H4B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
K1 O1 C4 N7 -113.34(19) . . . 2_647 ?
K1 N3 C1 N5 -107.8(2) 1_455 . . 2_546 ?
K1 N3 C1 N5 148.26(19) . . . 2_546 ?
K1 N3 C1 C2 -29.8(3) . . . 2_646 ?
K1 N3 C1 C2 74.2(3) 1_455 . . 2_646 ?
K1 N6 C2 C1 18.7(3) 1_655 . . 2_656 ?
K1 N6 C2 C1 -66.0(3) . . . 2_656 ?
K1 N6 C2 N4 -162.24(17) 1_655 . . 2_656 ?
K1 N6 C2 N4 113.0(2) . . . 2_656 ?
C3 N6 C2 C1 -178.7(3) . . . 2_656 ?
C3 N6 C2 N4 0.3(3) . . . 2_656 ?
N1 N3 C1 N5 0.2(3) 1_455 . . 2_546 ?
N1 N3 C1 C2 -177.8(3) 1_455 . . 2_646 ?
N6 C3 N7 N4 -0.7(3) . . . 2_656 ?
N6 C3 N7 C4 179.4(2) . . . 2_657 ?
N5 N2 N1 K1 72.1(3) 2_646 . . . ?
N5 N2 N1 N3 0.3(4) 2_646 . . 1_655 ?
N7 C3 N6 K1 146.3(2) . . . 1_655 ?
N7 C3 N6 K1 -123.3(2) . . . . ?
N7 C3 N6 C2 0.2(3) . . . . ?

_iucr_refine_instructions_details 
;
TITL BWN19354 in P2(1)
    bwn19354.res
    created by SHELXL-2018/3 at 17:46:00 on 10-Jul-2019
CELL 0.71073 3.9924 12.1919 7.7023 90 95.441 90
ZERR 2 0.0008 0.0024 0.0015 0 0.03 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H K N O
UNIT 8 8 2 14 2

L.S. 4
PLAN  5
SIZE 0.15 0.14 0.1
TEMP -110
FREE K1 C3
ACTA
BOND $H
CONF
fmap 2
REM <olex2.extras>
REM <HklSrc "%.\\BWN19354.hkl">
REM </olex2.extras>

WGHT    0.047700    0.079200
FVAR      17.26298
K1    3    0.395777    0.902240    0.661105    11.00000    0.02507    0.01427 =
         0.01642   -0.00101    0.00086   -0.00346
O1    5    0.364129    0.905813    1.014668    11.00000    0.02758    0.01596 =
         0.01367    0.00116    0.00574    0.00358
AFIX   3  0.8400
H1    2    0.312919    0.954643    1.084398    11.00000   -1.20000
AFIX   0
N3    4   -0.070469    0.725228    0.662995    11.00000    0.02222    0.01491 =
         0.01403   -0.00032    0.00525   -0.00187
C3    1    0.657990    1.147451    0.854962    11.00000    0.02184    0.01302 =
         0.01643    0.00139    0.00317   -0.00332
AFIX  43
H3    2    0.598670    1.118012    0.962066    11.00000   -1.20000
AFIX   0
N2    4    0.794643    0.564080    0.754028    11.00000    0.02914    0.01689 =
         0.01892    0.00173    0.00413   -0.00500
C1    1   -0.001003    0.647773    0.548391    11.00000    0.01671    0.01057 =
         0.01279   -0.00083   -0.00005   -0.00112
N1    4    0.801223    0.669467    0.792348    11.00000    0.02483    0.02005 =
         0.01456    0.00167    0.00510   -0.00396
N6    4    0.820122    1.092502    0.739646    11.00000    0.02058    0.01434 =
         0.01535    0.00022    0.00162   -0.00128
N4    4    0.287915    0.765937    0.357548    11.00000    0.01737    0.01571 =
         0.01113   -0.00036    0.00311    0.00048
N5    4    0.080794    1.047035    0.400327    11.00000    0.02770    0.01585 =
         0.01759   -0.00110    0.00297    0.00342
C2    1    0.845709    1.169115    0.611628    11.00000    0.01397    0.01137 =
         0.01541    0.00003   -0.00073   -0.00235
N7    4    0.589448    1.249943    0.799863    11.00000    0.01711    0.01380 =
         0.01259    0.00010    0.00428   -0.00119
C4    1    0.586666    0.837897    1.115786    11.00000    0.01743    0.01747 =
         0.01764    0.00167    0.00553    0.00002
AFIX  23
H4A   2    0.716042    0.882472    1.206321    11.00000   -1.20000
H4B   2    0.748188    0.805100    1.040783    11.00000   -1.20000
AFIX   0
HKLF 4




REM  BWN19354 in P2(1)
REM wR2 = 0.0738, GooF = S = 1.042, Restrained GooF = 1.041 for all data
REM R1 = 0.0279 for 1600 Fo > 4sig(Fo) and 0.0281 for all 1614 data
REM 118 parameters refined using 1 restraints

END  
     
WGHT      0.0477      0.0792 

REM Highest difference peak  0.217,  deepest hole -0.276,  1-sigma level  0.057
Q1    1   0.9366  1.1574  0.5408  11.00000  0.05    0.22
Q2    1   0.3275  0.9628  0.4176  11.00000  0.05    0.20
Q3    1   0.2062  0.8620  0.8691  11.00000  0.05    0.20
Q4    1   0.0325  0.9532  1.2031  11.00000  0.05    0.19
Q5    1   0.7712  0.8959  1.0115  11.00000  0.05    0.19

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0279 for 1600 Fo > 4sig(Fo) and 0.0281 for all 2465 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.22, deepest hole -0.28
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0281
  REM R1_gt = 0.0279
  REM wR_ref = 0.0738
  REM GOOF = 1.042
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 2465
  REM Reflections_gt = 1600
  REM Parameters = n/a
  REM Hole = -0.28
  REM Peak = 0.22
  REM Flack = 0.09(3)

  
;
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bwn19353
_database_code_depnum_ccdc_archive 'CCDC 1993946'
loop_
_audit_author_name
_audit_author_address
'Xiaoming Yang'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2020-03-31 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;
_audit_creation_date             2019-07-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H6 N7 Na O2'
_chemical_formula_sum            'C4 H6 N7 Na O2'
_chemical_formula_weight         207.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.0784(16)
_cell_length_b                   7.1115(14)
_cell_length_c                   13.838(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.05(3)
_cell_angle_gamma                90
_cell_volume                     787.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2609
_cell_measurement_temperature    163(2)
_cell_measurement_theta_max      27.4778
_cell_measurement_theta_min      1.4862
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5265
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         2.763
_diffrn_ambient_temperature      163.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1705
_reflns_number_total             1789
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1789
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0433
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+0.5280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1105
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O1(H1A,H1B), O2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Na1 Na -0.07671(8) 0.76105(10) 0.52356(5) 0.0217(2) Uani 1 1 d . . . . .
O1 O -0.00783(15) 1.05965(18) 0.60742(8) 0.0206(3) Uani 1 1 d . . . . .
H1A H 0.036400 1.041301 0.665280 0.025 Uiso 1 1 d R . . . .
H1B H -0.105850 1.100971 0.604290 0.025 Uiso 1 1 d R . . . .
O2 O -0.17588(14) 0.64616(18) 0.66191(8) 0.0194(3) Uani 1 1 d . . . . .
H2 H -0.280680 0.646854 0.649449 0.023 Uiso 1 1 d R . . . .
N1 N 0.22398(18) 0.6466(2) 0.55347(10) 0.0214(3) Uani 1 1 d . . . . .
N2 N 0.22607(19) 0.5757(2) 0.64438(11) 0.0243(4) Uani 1 1 d . . . . .
N3 N 0.38084(18) 0.5706(2) 0.68902(10) 0.0213(3) Uani 1 1 d . . . . .
N4 N 0.48476(17) 0.6372(2) 0.62885(10) 0.0174(3) Uani 1 1 d . . . . .
N5 N -0.05693(16) 0.6009(2) 0.82604(9) 0.0150(3) Uani 1 1 d . . . . .
N6 N -0.16024(17) 0.6726(2) 0.88665(9) 0.0153(3) Uani 1 1 d . . . . .
N7 N -0.38945(17) 0.7972(2) 0.45412(10) 0.0174(3) Uani 1 1 d . . . . .
C1 C 0.3851(2) 0.6825(2) 0.54711(11) 0.0155(3) Uani 1 1 d . . . . .
C2 C -0.3988(2) 0.8792(2) 0.36704(12) 0.0182(3) Uani 1 1 d . . . . .
H2A H -0.304770 0.918373 0.337932 0.022 Uiso 1 1 calc R . . . .
C3 C -0.1233(2) 0.5118(2) 0.73299(11) 0.0169(3) Uani 1 1 d . . . . .
H3A H -0.035655 0.432130 0.710600 0.020 Uiso 1 1 calc R . . . .
H3B H -0.218715 0.429863 0.742582 0.020 Uiso 1 1 calc R . . . .
C4 C -0.0543(2) 0.7326(2) 0.96219(11) 0.0144(3) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Na1 0.0179(4) 0.0296(4) 0.0176(4) 0.0049(3) 0.0029(3) 0.0025(3)
O1 0.0155(6) 0.0308(7) 0.0152(6) 0.0018(5) 0.0018(4) 0.0038(5)
O2 0.0154(6) 0.0273(7) 0.0147(6) 0.0040(5) -0.0005(4) -0.0003(5)
N1 0.0170(7) 0.0300(8) 0.0174(7) 0.0049(6) 0.0034(5) 0.0020(6)
N2 0.0202(8) 0.0349(9) 0.0181(7) 0.0057(6) 0.0042(6) 0.0023(7)
N3 0.0205(7) 0.0285(8) 0.0151(7) 0.0021(6) 0.0029(6) 0.0003(6)
N4 0.0176(7) 0.0212(7) 0.0131(6) 0.0008(5) 0.0009(5) -0.0003(6)
N5 0.0144(7) 0.0188(7) 0.0117(6) -0.0007(5) 0.0011(5) -0.0004(5)
N6 0.0143(6) 0.0194(7) 0.0123(6) -0.0006(5) 0.0019(5) -0.0002(5)
N7 0.0146(7) 0.0225(7) 0.0147(7) 0.0012(5) 0.0007(5) 0.0006(6)
C1 0.0153(8) 0.0169(8) 0.0138(7) -0.0013(6) 0.0008(6) 0.0015(6)
C2 0.0157(8) 0.0220(8) 0.0166(8) 0.0002(6) 0.0018(6) -0.0013(7)
C3 0.0201(8) 0.0183(8) 0.0118(7) -0.0004(6) 0.0000(6) -0.0019(6)
C4 0.0149(8) 0.0155(7) 0.0124(7) 0.0023(6) 0.0011(6) -0.0007(6)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Na1 Na1 3.9967(16) 3_566 ?
Na1 Na1 3.7065(16) 3_576 ?
Na1 O1 2.3926(14) 3_576 ?
Na1 O1 2.4463(16) . ?
Na1 O2 2.3246(14) . ?
Na1 N1 2.5403(17) . ?
Na1 N7 2.5870(17) . ?
O1 H1A 0.8400 . ?
O1 H1B 0.8400 . ?
O2 H2 0.8400 . ?
O2 C3 1.3941(19) . ?
N1 N2 1.353(2) . ?
N1 C1 1.341(2) . ?
N2 N3 1.315(2) . ?
N3 N4 1.349(2) . ?
N4 C1 1.333(2) . ?
N5 N6 1.3624(18) . ?
N5 C2 1.331(2) 4_676 ?
N5 C3 1.467(2) . ?
N6 C4 1.325(2) . ?
N7 C2 1.331(2) . ?
N7 C4 1.369(2) 4_575 ?
C1 C4 1.465(2) 4_675 ?
C2 H2A 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Na1 Na1 Na1 134.76(4) 3_576 3_566 ?
O1 Na1 Na1 104.09(4) 3_576 3_566 ?
O1 Na1 Na1 145.96(5) . 3_566 ?
O1 Na1 Na1 40.54(3) 3_576 3_576 ?
O1 Na1 Na1 39.47(3) . 3_576 ?
O1 Na1 O1 80.02(5) 3_576 . ?
O1 Na1 N1 92.98(5) . . ?
O1 Na1 N1 85.77(5) 3_576 . ?
O1 Na1 N7 91.89(5) 3_576 . ?
O1 Na1 N7 103.61(5) . . ?
O2 Na1 Na1 87.61(4) . 3_566 ?
O2 Na1 Na1 129.01(5) . 3_576 ?
O2 Na1 O1 168.25(6) . 3_576 ?
O2 Na1 O1 89.78(5) . . ?
O2 Na1 N1 100.67(5) . . ?
O2 Na1 N7 84.82(5) . . ?
N1 Na1 Na1 89.24(4) . 3_576 ?
N1 Na1 Na1 54.38(4) . 3_566 ?
N1 Na1 N7 162.60(6) . . ?
N7 Na1 Na1 109.93(5) . 3_566 ?
N7 Na1 Na1 100.17(4) . 3_576 ?
Na1 O1 Na1 99.98(5) 3_576 . ?
Na1 O1 H1A 132.6 3_576 . ?
Na1 O1 H1A 110.8 . . ?
Na1 O1 H1B 98.1 3_576 . ?
Na1 O1 H1B 97.4 . . ?
H1A O1 H1B 112.1 . . ?
Na1 O2 H2 106.4 . . ?
C3 O2 Na1 135.71(10) . . ?
C3 O2 H2 110.3 . . ?
N2 N1 Na1 99.09(10) . . ?
C1 N1 Na1 147.46(12) . . ?
C1 N1 N2 104.24(14) . . ?
N3 N2 N1 109.53(14) . . ?
N2 N3 N4 109.46(13) . . ?
C1 N4 N3 104.75(13) . . ?
N6 N5 C3 121.44(13) . . ?
C2 N5 N6 109.38(13) 4_676 . ?
C2 N5 C3 129.13(14) 4_676 . ?
C4 N6 N5 102.86(13) . . ?
C2 N7 Na1 107.97(11) . . ?
C2 N7 C4 102.08(13) . 4_575 ?
C4 N7 Na1 149.90(11) 4_575 . ?
N1 C1 C4 124.56(15) . 4_675 ?
N4 C1 N1 112.01(14) . . ?
N4 C1 C4 123.39(15) . 4_675 ?
N5 C2 N7 111.22(14) 4_575 . ?
N5 C2 H2A 124.4 4_575 . ?
N7 C2 H2A 124.4 . . ?
O2 C3 N5 111.17(14) . . ?
O2 C3 H3A 109.4 . . ?
O2 C3 H3B 109.4 . . ?
N5 C3 H3A 109.4 . . ?
N5 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
N6 C4 N7 114.45(14) . 4_676 ?
N6 C4 C1 120.94(15) . 4_576 ?
N7 C4 C1 124.58(15) 4_676 4_576 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Na1 O2 C3 N5 106.66(15) . . . . ?
Na1 N1 N2 N3 -157.07(12) . . . . ?
Na1 N1 C1 N4 134.55(18) . . . . ?
Na1 N1 C1 C4 -43.4(3) . . . 4_675 ?
Na1 N7 C2 N5 178.83(11) . . . 4_575 ?
N1 N2 N3 N4 -0.2(2) . . . . ?
N2 N1 C1 N4 0.07(19) . . . . ?
N2 N1 C1 C4 -177.89(15) . . . 4_675 ?
N2 N3 N4 C1 0.19(19) . . . . ?
N3 N4 C1 N1 -0.16(19) . . . . ?
N3 N4 C1 C4 177.83(15) . . . 4_675 ?
N5 N6 C4 N7 -0.39(18) . . . 4_676 ?
N5 N6 C4 C1 -178.55(14) . . . 4_576 ?
N6 N5 C3 O2 78.18(18) . . . . ?
C1 N1 N2 N3 0.05(19) . . . . ?
C2 N5 N6 C4 0.01(17) 4_676 . . . ?
C2 N5 C3 O2 -104.36(19) 4_676 . . . ?
C3 N5 N6 C4 177.92(14) . . . . ?
C4 N7 C2 N5 0.58(18) 4_575 . . 4_575 ?

_iucr_refine_instructions_details 
;
TITL bwn19353 in P2(1)/n
    bwn19353.res
    created by SHELXL-2018/3 at 10:43:18 on 09-Jul-2019
CELL 0.71073 8.0784 7.1115 13.838 90 98.049 90
ZERR 4 0.0016 0.0014 0.0028 0 0.03 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N Na O
UNIT 16 24 28 4 8

L.S. 4
PLAN  5
SIZE 0.13 0.12 0.1
TEMP -110
BOND $H
fmap 2
acta
CONF
REM <olex2.extras>
REM <HklSrc "%.\\bwn19353.hkl">
REM </olex2.extras>

WGHT    0.048100    0.528000
FVAR       8.89321
NA1   4   -0.076715    0.761051    0.523565    11.00000    0.01789    0.02964 =
         0.01760    0.00489    0.00292    0.00249
O1    5   -0.007830    1.059651    0.607420    11.00000    0.01553    0.03080 =
         0.01521    0.00182    0.00176    0.00375
AFIX   3  0.8400
H1A   2    0.036400    1.041301    0.665280    11.00000   -1.20000
H1B   2   -0.105850    1.100971    0.604290    11.00000   -1.20000
AFIX   0
O2    5   -0.175881    0.646164    0.661909    11.00000    0.01536    0.02726 =
         0.01471    0.00402   -0.00046   -0.00030
AFIX   3  0.8400
H2    2   -0.280680    0.646854    0.649449    11.00000   -1.20000
AFIX   0
N1    3    0.223982    0.646599    0.553471    11.00000    0.01700    0.02998 =
         0.01742    0.00491    0.00344    0.00200
N2    3    0.226067    0.575722    0.644377    11.00000    0.02022    0.03494 =
         0.01807    0.00573    0.00425    0.00231
N3    3    0.380844    0.570555    0.689020    11.00000    0.02051    0.02847 =
         0.01513    0.00209    0.00288    0.00032
N4    3    0.484760    0.637249    0.628848    11.00000    0.01764    0.02125 =
         0.01308    0.00077    0.00088   -0.00031
N5    3   -0.056927    0.600893    0.826038    11.00000    0.01440    0.01877 =
         0.01167   -0.00071    0.00108   -0.00038
N6    3   -0.160236    0.672607    0.886648    11.00000    0.01431    0.01937 =
         0.01228   -0.00060    0.00186   -0.00020
N7    3   -0.389454    0.797247    0.454116    11.00000    0.01460    0.02250 =
         0.01466    0.00118    0.00072    0.00061
C1    1    0.385101    0.682467    0.547107    11.00000    0.01532    0.01694 =
         0.01379   -0.00129    0.00085    0.00153
C2    1   -0.398797    0.879190    0.367037    11.00000    0.01574    0.02197 =
         0.01663    0.00016    0.00183   -0.00130
AFIX  43
H2A   2   -0.304770    0.918373    0.337932    11.00000   -1.20000
AFIX   0
C3    1   -0.123310    0.511833    0.732986    11.00000    0.02007    0.01829 =
         0.01182   -0.00044   -0.00002   -0.00186
AFIX  23
H3A   2   -0.035655    0.432130    0.710600    11.00000   -1.20000
H3B   2   -0.218715    0.429863    0.742582    11.00000   -1.20000
AFIX   0
C4    1   -0.054320    0.732586    0.962191    11.00000    0.01491    0.01554 =
         0.01240    0.00230    0.00109   -0.00066
HKLF 4




REM  bwn19353 in P2(1)/n
REM wR2 = 0.1105, GooF = S = 1.106, Restrained GooF = 1.106 for all data
REM R1 = 0.0433 for 1705 Fo > 4sig(Fo) and 0.0458 for all 1789 data
REM 127 parameters refined using 0 restraints

END  
     
WGHT      0.0481      0.5280 

REM Highest difference peak  0.312,  deepest hole -0.253,  1-sigma level  0.062
Q1    1  -0.0947  0.7635  1.0020  11.00000  0.05    0.31
Q2    1  -0.1168  0.6226  0.8569  11.00000  0.05    0.28
Q3    1  -0.0972  0.5607  0.7829  11.00000  0.05    0.26
Q4    1  -0.4655  0.7842  0.4618  11.00000  0.05    0.21
Q5    1  -0.0378  0.4881  0.7197  11.00000  0.05    0.20

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0433 for 1705 Fo > 4sig(Fo) and 0.0458 for all 5561 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.31, deepest hole -0.25
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0458
  REM R1_gt = 0.0433
  REM wR_ref = 0.1105
  REM GOOF = 1.106
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 5561
  REM Reflections_gt = 1705
  REM Parameters = n/a
  REM Hole = -0.25
  REM Peak = 0.31
  REM Flack = n/a

  
;
_olex2_submission_special_instructions 'No special instructions were received'
